3'-N,N-didemethyl-6-O-methyl-9a-aza-9a-homoerythromycin A | 1376295-82-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3'-N,N-didemethyl-6-O-methyl-9a-aza-9a-homoerythromycin A
• 英文别名: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-amino-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4-dihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-10-methoxy-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecane-7,15-dione
• CAS: 1376295-82-7
• 化学式: C₃₆H₆₆N₂O₁₃
• 分子量: 734.926
• InChiKey: SODALHMNVZHUEP-DBOMZMBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  51
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  218
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  3'-N,N-didemethyl-6-O-methyl-9a-aza-9a-homoerythromycin A 在 四丁基碘化铵 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 3'-N,N-didemethyl-2'-O,3'-N-carbonyl-3'-N-propyl-6-O-methyl-9a-aza-9a-homoerythromycin A
  参考文献：
  名称：

  Novel desosamine-modified 14- and 15-membered macrolides without antibacterial activity

  摘要：

  Novel modifications of the desosamine sugar of 14- and 15-membered antibacterial macrolides, in which the desosamine was fused with N-substituted-1,3-oxazolidin-2-ones, were developed in order to completely suppress antibacterial activity and make them promising agents for other biological targets. The synthesis of such bicyclic desosamine derivatives, especially 1,3-oxazolidin-2-one formation, was optimized and conducted under mild conditions without a need for protection/deprotection steps for other functional groups. A focused series of novel desosamine-modified macrolide derivatives was prepared and their antibacterial activities tested. It was shown that these macrolide derivatives do not possess any residual antibacterial activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.076
• 作为产物：
  描述：

  3'-N-demethyl-6-O-methyl-9a-aza-9a-homoerythromycin A 在 碘 、 sodium methylate 、 三羟甲基氨基甲烷 作用下， 以 甲醇 为溶剂， 以45%的产率得到3'-N,N-didemethyl-6-O-methyl-9a-aza-9a-homoerythromycin A
  参考文献：
  名称：

  Novel desosamine-modified 14- and 15-membered macrolides without antibacterial activity

  摘要：

  Novel modifications of the desosamine sugar of 14- and 15-membered antibacterial macrolides, in which the desosamine was fused with N-substituted-1,3-oxazolidin-2-ones, were developed in order to completely suppress antibacterial activity and make them promising agents for other biological targets. The synthesis of such bicyclic desosamine derivatives, especially 1,3-oxazolidin-2-one formation, was optimized and conducted under mild conditions without a need for protection/deprotection steps for other functional groups. A focused series of novel desosamine-modified macrolide derivatives was prepared and their antibacterial activities tested. It was shown that these macrolide derivatives do not possess any residual antibacterial activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.076

文献信息

• Novel desosamine-modified 14- and 15-membered macrolides without antibacterial activity
  作者：Ivana Palej Jakopović、Mirjana Bukvić Krajačić、Maja Matanović Škugor、Vlado Štimac、Dijana Pešić、Ines Vujasinović、Sulejman Alihodžić、Hana Čipčić Paljetak、Goran Kragol

  DOI：10.1016/j.bmcl.2012.03.076

  日期：2012.5

  Novel modifications of the desosamine sugar of 14- and 15-membered antibacterial macrolides, in which the desosamine was fused with N-substituted-1,3-oxazolidin-2-ones, were developed in order to completely suppress antibacterial activity and make them promising agents for other biological targets. The synthesis of such bicyclic desosamine derivatives, especially 1,3-oxazolidin-2-one formation, was optimized and conducted under mild conditions without a need for protection/deprotection steps for other functional groups. A focused series of novel desosamine-modified macrolide derivatives was prepared and their antibacterial activities tested. It was shown that these macrolide derivatives do not possess any residual antibacterial activity. (C) 2012 Elsevier Ltd. All rights reserved.